Copper-mediated three-component synthesis of 2-trifluoromethyl benzimidazoles?
Organic Chemistry Frontiers Pub Date: 2022-04-28 DOI: 10.1039/D2QO00285J
Abstract
A copper-mediated three-component reaction of o-iodoanilines, anilines, and ethyl trifluoropyruvate is reported. The transformation allows diverse substrate scope on both o-iodoanilines and anilines, delivering various 2-trifluoromethylbenzimidazole products in moderate to good yields. Mechanistic studies suggest that this transformation proceeds via condensation of o-iodoaniline with ethyl trifluoropyruvate, followed by an intermolecular Ullmann-type cross-coupling reaction with aniline and intramolecular amination.
Recommended Literature
- [1] Excitation energies from ground-state density-functionals by means of generator coordinates A. B. F. da Silva,K. CapellePhys. Chem. Chem. Phys., 2009,11, 4564-4569 10.1039/B902529D
- [2] Emulsion technologies for multicellular tumour spheroid radiation assays? Kay S. McMillan,Anthony G. McCluskey,Annette Sorensen,Marie Boyd,Michele ZagnoniAnalyst, 2016,141, 100-110 10.1039/C5AN01382H
- [3] Emerging enantiomeric resolution materials with homochiral nano-fabrications Ji-Ping WeiNanoscale, 2015,7, 11815-11832 10.1039/C5NR03048J
- [4] Enabling shape memory and healable effects in a conjugated polymer by incorporating siloxane via dynamic imine bond? Yaling Zhang,Chunhui Dai,Shiwei Zhou,Bin LiuChem. Commun., 2018,54, 10092-10095 10.1039/C8CC05410J
- [5] Embedding heteroatoms: an effective approach to create porphyrin-based functional materials Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro OsukaDalton Trans., 2017,46, 13322-13341 10.1039/C7DT02815F
- [6] Evolutionary de novo design of phenothiazine derivatives for dye-sensitized solar cells? Vishwesh Venkatraman,Marco Foscato,Vidar R. Jensen,Bj?rn K?re AlsbergJ. Mater. Chem. A, 2015,3, 9851-9860 10.1039/C5TA00625B
- [7] Fe/Fe3C@C nanoparticles encapsulated in N-doped graphene–CNTs framework as an efficient bifunctional oxygen electrocatalyst for robust rechargeable Zn–air batteries? Zhiyan Chen,Nan Wu,Yaobing Wang,Bing Wang,Yingde WangJ. Mater. Chem. A, 2018,6, 516-526 10.1039/C7TA08423D
- [8] Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals? Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael HardyAnalyst, 2019,144, 4194-4203 10.1039/C9AN00468H
- [9] Establishing plasmon contribution to chemical reactions: alkoxyamines as a thermal probe? Olga Guselnikova,Gérard Audran,Jean-Patrick Joly,Andrii Trelin,Evgeny V. Tretyakov,Vaclav Svorcik,Oleksiy Lyutakov,Sylvain R. A. MarqueChem. Sci., 2021,12, 4154-4161 10.1039/D0SC06470J
- [10] Evidence for the intrinsic nature of band-gap states electrochemically observed on atomically flat TiO2(110) surfaces? Shintaro Takata,Yoshihiro MiuraPhys. Chem. Chem. Phys., 2014,16, 24784-24789 10.1039/C4CP03280B
Journal Name:Organic Chemistry Frontiers
research_products
-
CAS no.: 89640-58-4